


【Lost In Wonderland】

by Randomfanner



Series: Tales from Wonderland [2]
Category: Twisted-Wonderland (Video Game)
Genre: Accidental Knotting, Aphrodisiacs, Biting, Blindfolds, Blood, Blood Kink, Blow Jobs, Bondage, Choking, Closet Sex, Cock Warming, Collars, Come Swallowing, Contracts, Control, Cuddling & Snuggling, Desk Sex, Dirty Talk, Double Penetration, Dubious Consentacles, Eventual Happy Ending, Exhibitionism, Extremely Dubious Consent, F/M, Facials, Fae & Fairies, Femdom, Fights, Fluff and Angst, Fluff and Smut, Fluffy Ending, Food Kink, Foursome - F/M/M/M, Freaky Tongue, Hair-pulling, Japanese Rope Bondage, Kidnapping, Knotting, Light Angst, Light Bondage, Lingerie, Loss of Virginity, Love Bites, Loving Marriage, Marking, Mating, Mildly Dubious Consent, Mirror Sex, Multiple Orgasms, Multiple Yanderes, Non-Consensual Tickling, Oral Sex, Orgasm Delay/Denial, Overstimulation, Pet Names, References to Ouran High School Host Club, Rescue, Rescue Missions, Sadism, Safewords, Sex Toys, Shameless Smut, Smut, Smut because Smut Fic, Soft sex, Spitroasting, Strawberries, Sweet, Teacher-Student Relationship, Teasing, Teeth, Temperature Play, Tentacle Sex, Tentacles, Threesome - F/M/M, Tickling, Triple Penetration, Twins, Under-Desk Blow Jobs, Vaginal Fingering, Vaginal Sex, Vibrators, Voyeurism, Wax Play, Whipped Cream, Wolf Sex, Yandere, strange penis
Language: English
Status: In-Progress
Published: 2020-04-14
Updated: 2020-07-18
Packaged: 2021-03-01 21:28:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 14
Words: 17,271
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23653861
Author URL: https://archiveofourown.org/users/Randomfanner/pseuds/Randomfanner
Summary: A smut collection based on Twisted Wonderland.
Relationships: Azul Ashengrotto/Floyd Leech/Jade Leech/Player, Azul Ashengrotto/Reader, Dire Crowley/Reader, Divus Crewel/Reader, Floyd Leech/Jade Leech/Reader, Floyd Leech/Reader, Floyd Leech/Reader/Jade Leech, Idia Shroud/Reader, Jack Howl/Reader, Jade Leech/Reader, Leona Kingscholar/Reader, Malleus Draconia/Reader, Riddle Rosehearts/Reader, Trey Clover/Reader, Vil Schoenheit/Reader
Series: Tales from Wonderland [2]
Series URL: https://archiveofourown.org/series/1751707
Comments: 71
Kudos: 770





	1. 【Posion Apple】

**Author's Note:**

> Vil decides to give you a sweet, crisp apple with...
> 
> A little something extra~

"I didn't see you at Breakfast today, are you alright?" Vil asked. You looked up from your notebook, doing just a bit of study before the history test.

"Huh? Oh! Yes, I... I had an extra lesson with Master Crewel in the morning," you explained, turning around to face him on the row of sits just behind your own. Vil shook his head, tsking a little bit as he did so. He pulled something out of his bag and tossed it down. You barely caught it and studied it. A red apple that shined in the light. 

"You cannot hope to perform well on an empty stomach! Honestly, for someone like yourself you think you would know better," he lightly scolded. You blushed and looked away, holding the apple in your hand. "I kept it for myself... but you need it more. It isn't much but it will hopefully tide you over till lunch," you nodded your head, giving him a small smile... 

What a cute, adorable lips. 

"Thank you so much, Vil," you said, before you took your first bite of the apple. Vil smirked and nodded his head, trying not to chuckle.

"Any time, my darling~!" Any time at all....~ 

Vil watched you as you stood next to him, listening to Ashton's instruction... yet you were seemingly a little dazed. A smirk formed on his lips as he looked towards Ashton, raising his hand.

"yes Vil, what is it?" Ashton asked. 

"(Y/n) is looking a little sick, may I escort her to the nurse?" Ashton gave a hum and moved a little closer, studying the girl besides him. He gave a little nod of his head.

"She is looking a little red, sure, I don't need any student passing out on my watch!" he assured. "Bad way to build muscle, I assure you," he said with a nod of his head, shooing the two away. 

"V-Vil I feel fi-"

"No, no dear, no need to act like you aren't sick," he scoped you up into his arms, like any other Prince charming. "We don't want you pushing yourself to hard... but this is what happens when you don't eat a full breakfast," he scolded lightly. 

"V-Vil... I-I feel... hot...." you complained laying in his arms as they got into the school. He looked down at you and gave a smirk , everything was working according to his design.... Not that he was expecting anything else. He nodded his head and placed you down, letting you use his body to support him and put a hand on your head. 

"Hm... you don't seem to have a fever, where do you feel hot, my dear?" he asked, he already knew exactly what was going on... but having you admit what was wrong sent a shiver up his spine. She gave a small pant as she looked up at him.

"B-between my legs... I-I feel really... hot..." you whimpered out. Vil nodded his head a little.

"I know exactly how to take care of something like this..." he picked you up again with a smirk on his face. 

"W-why are we in a br- mph" before you could finish the question Vil shoved his lips onto yours, you could taste the apple lip gloss he had applied. He grabbed your ass making you give a gasp as he forced his tongue inside... You gave a small moan and tangled one of your hands in his hair. He chuckled in the kiss, feeling around your mouth. He pulled away for a moment looking into your eyes. 

"You taste lovely my dear, just like the sweetest apple," he purred into your ear. "I wonder what else... tastes sweet~" he purred and removed your pants, letting them drop the floor. He got on his hands and knees. You covered you mouth, trying to keep quiet. Vil chuckled and traced his finger over the wet stop on your panties... That aphrodisiac he had implanted into the apple was working wonders~! He dragged a finger up and hook it underneath and pulled them down till they pooled at the bottom with your pants. He looked up and smirked and started to suck your clit. A moan left your lips making him chuckle. He slipped his middle and pointer in, starting to work to on stretching your cunt out. A moan left your lips as you used the wall of the broom closest for support. 

"V-Vil~!"

Oh, that did it, that did it for sure. He started to pick up the pace with his fingers, adding his tongue into the mix feeling around your pussy. You moaned on the wall making him chuckle, sending vibrations into you. 

'Cum for me, baby girl, cum for me~" he purred before putting his tongue back in. You gasped and moaned. He curled his fingers, moving right into a special little spot causing a gasp followed by the flood gates to open. he smirked and moved away, letting the fluid drip onto your panties. "perfect~" he purred into your ear before unbuckling his pants. 

"V-Vil I-"

"Are a virgin, and I plan on being gentle with you," he pulled you into another kiss as he stepped out of his pants and then his boxers. He was already rock hard and precum was pouring out. You looked down and whimpered as he lined his penis up with your opening and slowly entered. You gripped onto his shoulders shaking a little. He cooed soft things into your ear, you relaxed against him as he bottomed out, shaking from how good and almost over powering it felt. He smirked and started to move, at a slow teasing pace simply watching your face twist and contort in the pleasure he was giving to you. 

"P-please, f-faster V-Vil," he smirked and shook his head leaning closer to her.

"Vil?" he asked and gave a hard upward thrust, but stopped. "How about we try 'Master' Vil?"

"M-master Vil," you gasped out making him smirk, nodding his head. He grabbed your hip and started to thrust in and out quickly and rhythmically, you gasped and gripped his shoulders, panting against him. He moved a hand down and started to rub your clit. He whispered things in your ear as he finally found the spot he was looking for, given your slightly louder moans. He removed his other hand from your hip and forced it into your mouth.

"We don't want us getting to loud, now do we~?" he asked. All you could do was whimper and nod your head as he picked up the pace. If it weren't for his fingers gagging you things would have been a lot louder. 

You whimpered loudly and squeezed him, much tighter than before. He smirked and gave a small groan as he felt you cumming around his dick. Suddenly, he pulled out and forced you on your knees. Very out of it do to your orgasm you looked up at him as he pumped his dick, shooting right out onto your face. He looked down at you with a smirk on his face. 

"I'll get something to clean you up~!" he said with a smirk. God you looked wonderful like that. "We will have to do this more often~"

All you could do was give a little nod, dazed from the pleasure you had just received.


	2. 【Seasonal】

**Summary for the Chapter:**

> Leona has been following you around a lot.
> 
> I wonder why.

"Hey... you have a follower," Ace whispered to you. You only gave a small nod and a sigh.

"I am aware... I don't know what to do about it though," you whispered back. Leona stood behind a pillar, narrowing his eyes a little as he watched you walk with three morons you called your friends. The whispering wasn't as quiet as you would have thought. He moved behind the pillar and took a deep breath. 

Curse you, curse you and your cycles. 

"He does this every month... and I am not completely sure why..." you explained. You looked at Grim. "Do you have any idea what is going on? You are a cat after all," Grim gave a loud, clearly offended, gasp as you stated that and crossed his arms.

"No, I am not just a common cat! I wouldn't know what is going on," he stated and shook his head. "Besides, he is a big cat, what every is going on, even if I WAS a common cat, I probably couldn't help," he stated, looking away from the trio. Deuce gave a sigh and shrugged.

"I am sure what ever it is, it will pass," he assured. You nodded your head. You certainly hoped he would stop doing this and just tell you what was wrong.

"(Y/n), be a good pup and go fetch me some these herbs and mushrooms from the botanical garden now would you," Crewel asked. You looked up and nodded your head as you took the list he had in his hands. They should be easy enough to go grab! 

"Yes Master Crewel sir!" you said, giving a nod before you left the class room to go to the garden....

And a certain lion's favorite hang out spot.

"Hm, just need to get these frozen toadstools and I should be all good to go back to class!" you said with a grin on your face. You started to walk closer to where you thought they might be only to have your leg grabbed and you dragged into a bush, pinned down. "Wah-" before you could finish your lips were being stolen in a hot, passionate kiss. A hand ripped down your pants and panties with one movement. He pulled away and bite your shoulder, causing a loud squeal. "Leona?!" was all you could get out before he stole another kiss from you, blood dripping down your shoulder from the bite. 

"You don't know what you have been doing to me. Damn you," he muttered quietly before kissing you again. You looked at him bewildered, pulling away quickly.

"Leona, what do you mean?" you asked. He growled and held your hips down so you couldn't flip over to face him completely. 

"Male lion's don't have set cycles, they mate when their chosen female is fertile," he purred into your ear, using one his his hands to get his dick out. You whimpered feeling him rub it against you, it felt very strange.... with an odd texture. He noticed the confusion on your face and chuckled, moving closer. "You should be grateful, lions tend to have barbed penises... I do not, instead, it is more... dotted~" he purred into your ear before shoving it in your pussy. 

You gave a gasp of pain and grabbed onto the floor. He bottomed up, being a bit rougher with you than he should be. He noticed your expression of pain once he bottomed out and stopped, allowing you to adjust to the oddly shaped intrusion.

"You will feel very good soon~" he assured and started to whisper other dirty things into your ear. He slowly started to move his hips, dragging a moan from your mouth as he started to work on you, slowly but surely. Before long however, he was going at a lion's pace. You cried and moaned, feeling him run the texture of his penis over your g-spot over and over again. He growled and bite down on the other side of your shoulder, making paralleled bites. He moved a hand down and pinched your clit, hard. That was the tipping point.

"I-I AAhhh Am c-cumming!" you gasped, clenching around him making the feeling of his dick all the more vivid. He growled and rubbed against you, reaching his end as well. You shuddered feeling his warm cum fill you. After a few minutes of resting like that he pulled out and dragged you closer into his hold. "Leona?" you asked tiredly... but he was already asleep. You sighed, deciding not to fight him and snuggled up closer to the warm lion.


	3. 【How Naughty】

**Summary for the Chapter:**

> Azul catches you reading something naughty.
> 
> He takes it upon himself to punish you~

Reading hentai during class wasn't something you say you did a lot, in fact it was very rarely you read such sinful things. 

Today was simply an acceptation to that rule. 

For you see, a friend had loaned you the manga due to your.... tastes in things... unconventional. But she wanted it back for her private use before the end of the day. So this would be your only chance to read it. Hidden away in your textbook as you faked listening to the lecture by Mr.Trein. A bit of a red blush came to your face when it started to depict what everyone really read hentai for. 

Behind you, a white hair male smirked. How very interesting... Very interesting in deed. He had to hold back a chuckle, how naughty, reading something like that in class. 

Suppose there was only one way to deal with something like that.

"How are you enjoying the... little novel so far~?" your friend asked in a teasing tone. Your cheeks flared up as you changed out of your gym clothing.

"I am enjoying it rather a lot, I am sure I will have it done by lunch," you assured, trying to hide your blush. She chuckled and nodded her head.

"Good, I just need it back by the end of the day, but feel free to reread it during your last class periods" she teased and left the locker room. You finished getting dress and looked around for it in your locker. Your eyes widen with panic as you went on your tip toes... It wasn't there, the hentai novel was missing from your locker. You gave a horrified gasp, what if you had left it in Mr. Trein's class?! He'd have your head for keeping something like that around. You exited the locker room and started to sprint down the hall way.

"You seem to be breaking all the rule today, now aren't you?" you stopped hearing a voice behind you. You turned around to see Azul. You swallowed and took a step back, you had talked with him and had to admit... he was rather handsome... But he had a reputation of where he went, trouble followed due to his contracts. He held up the hentai and flipped through it. "Some naughty stuff you seem interested in, little Angelfish~" he purred. 

"Please give that back, it is my friends and she will need it back after school," you begged trying to take it from him. He held it up, keeping it out of your reach and chuckled. 

"Of course I will give it back... if you sign a contract with me~" he purred. You look up at him and pout a little.

"Fine...." you mutter, knowing your friend would kill you if she found out you let her hentai get stolen.

He chuckled and pulled out a contract from his coat pocket, he had been waiting for the day he could do something like this... But he could have never expected it would work THIS perfectly and let him do some of the... ideas he had in store for you. You barely even glanced over the contract, signing your name at the bottom. He tossed the book to you and smirked down at you. 

"Be at the Lounge by 5 PM," he told you, before he left. You sighed and looked down at the hentai in your hands.

How did you get wrapped up in all of this? All you wanted to do was read some kinky hentai with out getting a virus on your phone. 

"Right through this door," Jade assured you. You had went to the lounge only to be lead around by Jade in front of what seemed to be the dorm leader's room.... Or, as you really should say. Azul's dorm room... You took a gulp, and then took a breathe, and then knocked on the door.

"Come in, (Y/n)," you heard his voice and walked into the room. Jade shut the door behind you before disappearing. You slowly stepped in, looking around the room before you felt something grab your leg. You nearly gave a scream before something wrapped around your mouth and dragged your closer to where these... these.... tentacles? He pulled you closer to him and wrapped one around your waist. Your cheeks turned red as you were able to tilt your head up and as you expected, it was Azul. Your cheeks turned a deeper red as you looked up at him. "Surprised?" he asked. All you could do was give a little nod. "Good, now, are you ready for a good night, my dear?" once again, all you could do was give a little nod. He smirked and rubbed one of his tentacles against your leg. It was a tad bit... different than the rest. He adjusted the one at your mouth so the tip was rubbing against your mouth. You opened it just a tad and he slipped it in with ease. 

He pulled down your pants and panties with his hand and rubbed your clit just a bit. You moaned around the appendage in your mouth making him chuckle. He gave your forehead a little kiss. He slipped the oddly shaped on in, getting a very loud moan around. 

You shuddered with pleasure, he felt so good. You were not expecting this to happen today. He rubbed around and smirked when you nearly screamed around him.

He had found what he was looking for. With another tentacle he used a sucker to start squeezing on your clit well the one inside you start to rub and torture you poor little g-spot. You squirmed and moaned around him. 

"Just enjoy this dear~ You will feel wonderful~" he assured as he started to pick up the pace with this blissful torture. He moved the one in your mouth just a tad bit deeper well the one inside your cunt made a harder thrust against your g-spot.

With a muffle scream you came. He moved all his tentacles away expect for the one around your waist as you came down from your high. You looked up at him sleepily and started to fall asleep.... Then you were thrown on the bed.

"No, no, no, We aren't done yet my dear~" he assured as he got on top of you. "We are anything but finished~"


	4. 【Gently】

**Summary for the Chapter:**

> Idia and you have some fun in the bed room.
> 
> He really wants to be gentle with you.

"Are you sure it isn't too tight?" Idia asked as he checked the binding around your wrist. You gave a small chuckle and nodded your head. "The blindfold isn't either right?" he asked, running a hand gently over your cheek. You simply gave a nod and rubbed your cheek against his hand.

"I will be fine, Idia, I am excited to try this with you," he swallowed and nodded his head, before moving away from the bed. He grabbed a few things off the table and came back over. He got on the edge of the bed. He poured some lube onto his fingers and started to gently stroke your inner lips, prodding them open with the cold fluid. You gave a small moan making him shutter from the sound. He slowly moved his fingers in and out, being sure to get everything he could reach covered in lube. He slowly pulled out, getting a whimper and a moan. He shuddered looking down at you, so cute and tied up like that... He pulled out egg vibrator and a roll of tape and set it up over your clit. You gave a small moan when you felt it get placed there. He taped it down, making certain it was not getting caught on any hair or anything before turning it on. Her heard her moan and slowly pulled out his dick from his boxers, pumping it up and down slowly. He got out the dildo and rubbed some lube on it.

"Are you read for the dildo?" he asked, lining it up with your whole. You gave a moan and a enthusiastic nod of the head. He swallowed and nodded before slowly pushing in, drawing a moan from your mouth. He turned it onto the lowest setting and watched you moan and squirm.

"I-Idia-! Higher!" you whimper. He nodded his head and turned it up to the next setting, taking it nice and slowly to make sure you were comfortable.

That was what he was most worried about.

You gave a small whine as you squirm. He panicked for a moment.

"Is everything OK?" he asked. You nodded your head.

"D-don't be so w-worried with this, p-please turn it higher," you begged. His cheeks turned red as he nodded his head, turning the dildo up a few settings.

"is that better?" he asked, slowly pumping his dick in his hand as he watched you, squirming in your binds and moaning for him. You gave a nod and moaned out his name. He shuttered looking at you, you were so beautiful. Sweat covering your (s/c) skin making it glisten in the blue light , the way you twitched under the pleasure. He shuttered and started to pump faster losing himself too it. He gave low, raspy groans as he came, shooting himself all over your stomach and breasts. 

You shuttered and chuckled a little, but it was quickly cut off by a moan of pleasure as you broke down yourself, juices spilling out onto the sheets. He laid down next to you, turning off the toys and removing them.

"You enjoyed yourself, right?" he asked as he unbound your hands. You gave a cheerful nod and kissed his forehead.

"You enjoyed yourself too, right?" he nodded his head and gave you a quick kiss. "How about you start a bath and I will change the sheets?"

"Yes... that sounds... nice,"


	5. 【Shopping】

**Summary for the Chapter:**

> You have some issues with panties.
> 
> Malleus decides to take you shopping to... help with the issue.

You gave a whimper as you held your panties in your hand. They had fought the good fought with daily washings... But it was not meant to last. You put them down and gave a sigh, this was the problem with being sent from an alternative dimension with nothing but the clothes on your back.

Well there was a lot of problems with that.

But one of the biggest was the fact you only had one pair of panties. And it being an all boy's school, they had some clothing you could wear, uniforms and such... but not really... undergarments. And as much as you would love to go shopping for it, it was a bit of an awkward request to the head master... so you didn't really have the guts to ask if he could give you some funds to buy panties. You gave a sigh and rubbed your face. What could you do now...? You sigh and got up. Well, it looks like you didn't have much of a choice in the matter. 

"Where are you going?" a voice asked. You jumped and turned around to see... that one boy. The one who just was walking around the dorm. You looked away.

"I.... I am not going... anywhere," you lied. He tsked a little and moved closer.

'No need to lie, I promise I will not judge," he assured as he walked closer. You tensed up and took a step back, tripping on a rock and looking up at him. He looked down at you and offered a hand. "Come now, cat got your tongue?" he asked. The more time you spent here the clearer it came he was not going to back down till you told him. You gave a small sigh and looked away.

"My panties broke..." you mumbled quietly, not loud enough for him to really ear. He looked down at you, a smirk on his face.

'Could you repeat that?" he asked, leaning down a bit closer. You could feel his hot breathe tickle your chin. You took the hand.

"My panties... broke, so I.... I want to ask master Crowley if he would... give me some money to buy some..." you mumbled, just loud enough for him to hear. He chuckled and picked you up.

"I will take you," he said, not really making it as an offer as it was more by... force. 

"O-oh, I couldn't possible a-ask you to do th-" before you could get much more out, he had already used some sort of magic to take you both to the magic mirror. 

"Have you ever been outside the college before?" Malleus asked as you two both walked down the hallway. You thought for a moment before nodding your head.

"yes, once, when the chandelier broke I was one of the ones who got a crystal to fix it. I went to the dwarf mines to look for a crystal," you explained. He nodded his head as you both stopped in front of a store. 

'Elizabeth's Secret' 

Malleus lead you in and looked down at you, a bit of a smirk on his face.

"What size are you?" he asked. You blushed a little and mumbled your pantie size. "Also what is your bust? May as well get some bras well we are here," he said and gave your chest a small squeeze. You gave a squeal and were about to scold him but he put a finger up to his lips. "Best not to look a gift horse in the mouth, now go sit over by the changing room... I will pick some things out.... and have you model of course~" your cheeks turned pink.

'W-wha? I-i-"

"Oh don't look so surprised, I did bring you here, didn't I? now you owe me something... and I think a little show like that might be just what I need~" you blushed and nodded, not really being able to fight him...You really needed these undergarments and bringing it up to the Headmaster would probably be... Painful at the very least.

"H-how many of these did you pick out?' you asked as you looked at him in frilly green and black panties. He smirked as he nodded his head.

"That was the last one," he assured. You nodded your head and started to remove that pair, putting your clothing back on.

Or well, you started too. 

Before you could he shoved you against the mirror. You gave a gasp giving the person behind you enough time to kiss you, shoving their tongue into your mouth. You looked to see Malleus who pulled away, a string of saliva connecting the two of you already after such a short kiss. He smirked and kissed your shoulder. 

"The show was just for taking you here, but paying for the underwear is.... a whole different matter of payment," he purred as he sat down on the bench, forcing you into his lap. He held you close with one hand and slipped a finger into you with the other. A gasp left your mouth before you gave a quiet moan. "Now, now, you don't want someone hearing you, it is best if you keep quiet," he warned. You could only give a nod as he kept fingering you, having to bite your lip to keep quiet. He rubbed your clit before pulling them out completely. You gave a whine looking up at him. He smirked and made you look into the mirror. "Already so needy~"

He lifted you up and inserted himself in. You had to hold back the cry and tried to look away. He put the fingers wet with your juices. He held your head in place with his fingers forcing you to both taste yourself and look as he debauched you. He started at a very slow pace before he started to slowly pick up the pace. You watched as your juices poured around his thick cock that moved in and out of you. You shuttered and stared at the scene. Almost forgetting it was yourself who was being fucked and debauched in such away. 

He chuckled as he looked at your expression in the mirror, rocking up at a faster pace. He mumbled something you couldn't make out and it felt like something was pinching and twisting your clit. You squirmed and whimpered, barely keeping this quiet with how blissful he made you feel.

"Come on baby, don't you want to cum for your new master~?" you shuttered at the phrasing. "Come on. be a good little whore and cum for me~' he ordered. You fell a part at such a few simple words. He chuckled looking at how much wetness poured down from your entrance down onto his dick. What a sight to behold~ After a few more thrusts he joined you in cumming. You panted as he let you go, falling to the floor. He chuckled looking at you before dressing you with just a tad bit of magic.

"Let's go pay and you can.... continue paying me back~" he purred. All you could do was nod as you got up.

"I-i would like that,"


	6. 【Extra Whipped Cream】

**Summary for the Chapter:**

> Riddle and You decide to have some fun
> 
> Don't forget the extra whipped cream~

You chuckled a little as you looked at your tiny boyfriend tied to the bed. Riddle acted all tough, being the dorm head... But underneath that he was such a sub that was so easy to control. He looked at you, his cheeks a bright red as you moved closer, slowly shaking the bottle of whipped cream.

"You remember the safe word, correct?' you asked as you walked over, opening the container of strawberries. Riddle nodded his head a little. "Good, do not hesitate to use it, my little king," you gave his forehead a kiss. He puffed up his cheeks and looked away. You chuckled and shook the bottle just a bit more before putting some whip cream on his nipples. He shuttered a little bit from the cool feeling. You looked up at him and grabbed two strawberries, per-cut to make things move along just a bit quicker as you placed them on his nipples, being held in place by the whipped cream. He looked at you with his silver eyes as you bent down, you smirked and started to clean his left nipple. He gasped and squirmed a bit, the warmness from your mouth in direct conflict with the cold whipped cream. You chuckled, sucking and giving it a tiny bit. He gave a yelp in surprise, but it wasn't pained at all. You moved to the other nipple and picked up the strawberry with your teeth. You held it over and kissed Riddle, the strawberry between your teeth. He took the strawberry, his side being covered in whipped cream and blushed. You giggled and moved back down, cleaning the remaining whip cream off. He gave a small shudder.

"You are.. very skilled with your mouth," he got out. You looked up and chuckled. Giving him another kiss.

'You have not seen anything yet~" you teased as you moved down, you shook the bottle again and started to wrap it around his dick. He gasped out loud and jerked upward into the cold feeling. You grabbed some strawberries and careful placed them on balls. You looked up at his face, contorted with the new feeling. You bent down and slowly started to suck the head, getting it clean before going down, taking him down your throat the salty per-cum mixing with the whipped cream. He gave a loud moan and bucked into your mouth. You chuckled and held his hips down, so he didn't squirm as much. He gave a small whine. 

"Hey, don't hold me down!" he exclaimed. You looked at him and chuckled.

"How cute, I think you are forgetting who is in control~" you purred started to only focus on the tip again. He gave a groan and whined a little. You chuckled and went down on him. You came up, eating the strawberries and licking the whip cream off before going back to the main dessert you were enjoying this evening. You started to lick up a trail that made him groan before you took down the thing down your throat, happily sucking away.

"A-ah~" Riddle moaned out. You chuckled, sending vibrations through his dick. You started to fondle his balls and that was the ticket. He moaned and came right into your mouth. You giggled and kept sucking. Riddle squirmed a little, not used to something like that. He bite his lip as your kept going. "A-ah, Sundae! Sundae!" as soon as he said the word you pulled off and used magic to unchain him.

"Are you OK?" you asked, kissing his cheek. He nodded his head.

"Just... a bit too much... at one time," he explained looking away. You smiled and kissed his forehead.

"I'll get a bath ready, help yourself to some strawberries, K?" he nodded his head, sitting up in bed, taking the little container. 

he was such a cute little Queen of Hearts.

**Notes for the Chapter:**

> Riddle is a sub, prove me wrong.


	7. 【Games】

**Summary for the Chapter:**

> The twins invite you for a game.
> 
> "Which one is Jade?"

**Notes for the Chapter:**

> Night Raven College Host Club anyone?

"The rules are simple shrimpy! My brother and I drink this," Floyd lifted up a small glass bottle, shaking it around a little bit. "To make us look completely identical, and then you have to guess which one of us is Jade!" Floyd explained with a grin on his face. You nodded your head a little. Jade smiled and gave your cheek a little kiss. 

"Any questions, Angelfish?" he asked with a little grin on his face. You nodded your head.

"I do have one, actually... what do I get if I guess correctly?" you asked, a cheeky grin on your face. The twins looked at each other, wide smirks growing on their face. They circled around you as you sat in the chair. You tried to follow them as they walked around you. 

"Well, my sweet dear, if you guess right, you will be rewarded," Jade gave you a kiss, it quickly turning into more. He pulled away, leaving you a bit dazed as you looked up at him.

"But if you guess wrong, you will be punished!" Floyd exclaimed before biting your shoulder. You gave a small squeal as he pulled away, licking a few droplets of blood off his lips. "Understand, Shrimpy?' Floyd asked as he joined his brother. You gave a nod before both brothers threw down their own part of the potion. They did look the exact same. Their eyes changed to be only yellow and the strand of hair that could be used to tell them a part was no longer their easy. Looking at them it was impossible to tell the difference. Hell, the only way she knew which was which was because of what happened before they took the potion.... 

"Now shut your eyes"

"No peeking~" you gave a giggle before nodding your head, shutting your eyes. You heard them shuffle around, not peeking not that it would probably matter at this point. A few switching around and you would have been lost.

"Alright dear Shrimpy!"

"Open your eyes~" you opened your eyes and stared at them for a moment. Where did the voices come from.....The voice closer to Jade's came from the right.... 

"Which one of us is Jade?" they asked in sync. You swallowed hard, you were certain.... but it was still nerve wrecking knowing you'd be punish if you got it wrong. 

"Right. Jade is the one on the right," before of the twins looked at each other, grin spreading on their faces. You didn't like that. You didn't like that one bit. 

"Wrong~" both sang out. You looked at them surprised before the one that had to be Floyd(given the fact you guessed him as Jade) was behind you.

"I do a good impression of my brother, don't I!" he said as he removed his tie, quickly binding your hand behinds your back with it. Jade smirked and gave your cheek a little kiss.

"We wouldn't be too rough...' he assured as he removed his tie, wrapping it around your eyes so you couldn't see.

"W-what is the punishment?" you squeaked out as you felt one of the twin's resting his head on your shoulder.

"Oh nothing too.... painful, a little unbearable if you ask some, but you will like it!" Floyd explained as he slurped up the blood from the wound. You gave a whimper nodding as you felt Jade get rid of your pants and panties. You felt a tongue rub right on your clit causing you to moan a little. Jade chuckled on the little bundle of nerves, gently gliding over it with his sharp teeth threatening you with just a simple movement. Floyd smirked and moved his fingers down, shoving them into your dripping pussy being careful not to get in the way of his twin. You shudder and gave a louder moan. Jade smirked and kept tasting your clit, clearly enjoying himself as he slurped and sucked away. You gasped and rolled your hips into his face. Floyd did not seem to enjoy you giving so much attention to his brother and curled his fingers, making you gasp out. He chuckled and started rubbing along your walls, looking for that special spot. Jade chuckled at his brothers actions. You gave a moan. Before a shorter yell as you felt Floyd touch you G-spot. Floyd grinned and started to abuse the spot. 

"I-i am close~" you whimpered out. And with that, it all stopped, both twins moved away. Floyd licking his fingers clean of your juice. You looked around bewildered. "W-wha-"

"Oh don't look so confused, Shrimpy! it was a punishment, remember?" Floyd said with a grin. Jade nodded his head.

"Now we have a job for Azul... but we will not leave you lonely," you heard the sound of ripping tape as something was strapped onto your clit. Soon some light vibration started.

"Be ready for when you come back! If you handled your punishment well you may be rewarded!" Floyd called out. "We love you!" and with that, you heard the door shut.


	8. 【Snack Time】

**Summary for the Chapter:**

> Trey catches you enjoying a mid night snack. 
> 
> He promises not to tell, for a snack of his own~

**Notes for the Chapter:**

> Trey appreciation time

You know you shouldn't be down here, it was long past lights out and if you were caught by Riddle... Well, it would be off with your head so to speak... But those midnight craving were hitting you, they were hitting you hard. You tip toed over to the fridge and carefully pulled out the left over tart. You licked your lips, Trey's baking was heavenly. You grab a knife and carefully cut a small slice, just small enough it would be hard to notice, but hopefully enough to fulfill your carving. Your mouth started to water as you looked down at the strawberry tart in your hands. You opened your mouth and just as your teeth nearly came down on the amazing little morsel, the lights flicked on. You tried to hide, but it was already far too late.

"(Y/n)? I never expected you to be such a rule breaker," you froze looking at how it was. Trey Clover, the vice dorm leader..... And... Well. Your boyfriend. 

Oh shit.

He chuckled at the look on your face and moved closer, boxing you in between the counter and himself. He gave you a kiss on the cheek. You blushed and looked away, giving him an opening to grab the little piece of tart out of your hand. He tilted your chin towards him and put one end of the tart into your mouth before taking a bite out of the other end. You quickly realized what was going on and started to nibble your way down the sweet treat, meeting him in the middle with a kiss. He pulled away and kissed your nose. He put the cover back on the tart, putting it back in the fridge before quickly washing the knife with some soap, drying it off and putting it back into the knife block. You watched him for a moment before slowly backing away.

"Where do you think you are going? You have broken multiple rules.... I will need to report you to Riddle," Trey said as he looked towards you. You froze and looked at him.

"Please, anything but him," you whine as you take his hand, looking up with pleading eyes. He looks down at you and taps his chin. 

"Hm.... well.... maybe if you.... give me something just as tasty as a piece of tart in return, I will agree~" he purred into your ear. You looked at him and nodded your had, pulling yourself onto the counter and pulling off your panties. Trey's cheeks turned bright red. That is not exactly what he was going for, but he will happily take that type if midnight snack. "You are alright with this, correct~ I will let you off with just a kiss~" he purred into your ear. You chuckled and kissed his cheek. 

"I am more then OK with this~" you said with a wanton smirk on your face. He nodded his head and lifted up your night gown and licked at your clit, just a tiny little . You covered your mouth and looked down at him. He chuckles, not being able to see your face, but he could picture your cute little expression contorted in pleasure. He chuckled a bit before he started to suck the little nub, extracting a small moan from you mouth. He chuckled and moved away from the little bundle of nerves, shoving his tongue inside of you. You gave a gasp and grabbed his hair from under the nightgown, forcing him down farther. Why did you have to be so cute? He kept licking around, hearing you moan and feeling you squirm. "Your tongue is amazing,' you moan out as you lean back on the counter. He pulled away.

"Don't get to loud love, we don't need us getting caught~" he reminded before going right back where he was. You covered your mouth, trying not to moan out, but it was barely working as his godly tongue hit all the right spots inside of you. Before you knew it, you were releasing you cum into his mouth. He smirked and started to lap it up, getting you all cleaned up before he stood up, unbuckling his pants letting his boxers and pants drop. "Should we stop here, or do you want to keep going~?' he asked into your ear. A shudder went up your spine.

Before you could reply, however.

CRASH

"WHAT ARE YOU TWO DOING!?" both of your head swiveled over to Riddle, standing in the door way, a glass cup now on the floor in shards.

**Notes for the Chapter:**

> He wanted warm milk.
> 
> He got scarred for life.


	9. 【Stay Still】

**Summary for the Chapter:**

> Crowley oh so bored with his daily work. 
> 
> You give him something to be entertained about

Dire Crowley sat in his office, filling out the monthly bills, making sure a big enough shipment of food would come in so there would be no shortages, the normal boring paperwork that came with being a Headmaster at a school like Night Raven College. Yet, even with how boring it was, he kept a grin on his face the whole time. Most of the time it was boring but for right now? He had something to... keep him good company~ He rocked his hips. He heard a choke from under the table and chuckled a little. You were oh so cute, all tied up so elaborately in such perfect, red string like a present . He petted your hair a little.

"Aren't I so gracious, allowing you to be so lewd during school," he said looking down at you with a small smirk on his face. "Of course you aren't allowed to move or do anything other than sit there with my cock in your mouth, but most would never let you get away with this sort of thing," he purred looking down at you. You had to send him a soft glare, you were doing this for his sake... You had to restrain from sighing around his larger than average girth. It was to be expected with someone like Dire, it was why you married the man. He turned his attention back to his paper, a mild grin on his face. A knock was heard on the door and you had to hold back your smirk. You were going to punish him for being such a damn egoistical little bird man. "Come in!" he called.

"Headmaster, sir, I would like to talk to you about Grim," that sounded like Trein's voice. Perfect~ He would have to be nice and subtle with him around~ You gave a sudden lick of the vein trail leading up to the tip. You felt his whole body shudder. 

"Ah yes, what about him, Trein?" Dire asked, his voice a tiny bit wavering as he spoke. Trein gave a small sigh and shook his head, taking a seat across the table from him. You could hear a meow from Lucius. 

"He is a trouble maker beyond your wildest belief! I believe a suspension is in order, maybe even expulsion" Trein stated. You started to bob your head around your husband's dick. He grabbed your hair, giving it a warning tug, but that did anything but stop you. If anything, it was encouragement. He couldn't do much against you with Trein right there. 

"Oh? P-Please do elaborate" Dire's voice wavered for a moment. That is just what you needed. You gave a low hum, that vibrated around but made no sound. Lucius gave a meow as Trein gave a sigh, so far not noticing Crowley's.... change in demeanor.

"Well, to start, he is constantly sleeping in my class. He never pays attention," Trein started. Crowley gave a small nod of his head before you sucked in your cheeks around his cock. He gave a harder tug on your hair, but you knew damn well he didn't want you to stop. His leg was wrapped around your back, bringing you closer. This was turning him on so much, not that he would ever admit it... or maybe the thought of what he was going to do to you as soon as Trein left was getting him so hard. "Not to mention, when he is awake he is causing trouble. At one point he sneezed on another students notes, lighting them on fire. He never apologized and was rather rude about it to both me and the student. Then, later Some times he even starts a fight with Lucius," 

"Have you talked to his supervisor about it? And have you given him punishment?" Crowley asked. He was doing such a good of keeping of keeping his voice all steady when he spoke, you gave a very silent chuckle around his dick, his hand jerked your hair harshly, yet pulled you closer. 

"His supervisor tries, I can tell. But they cannot control that beast, and nothing I seem to do sticks. I think threatening him with getting kicked out may knock some sense into him," Trein explained, Crowley nodded his head. 

"Of co-" he was forced to pause as you rubbed his teeth against him, not biting down but applying pressure. "OURSE!!!' he exclaimed a bit louder. Trein looked at him concerned.

"Are you alright sir?"

"Fine, fine" he cleared his throat "Just fine, I will take it into consideration and may suspend him," Crowley assured. "you are dismissed," he said. Trein nodded his head and left the room. As soon as the door shut Crowley dragged of you off him and threw you onto his desk, moving all the papers to the side. You smirked at him.

'What?" he growled at you and pounced onto you, He started to bite and suck on his neck, leaving very, very hard to hide marks. 

"You know exactly what, you naughty girl~" he purred, giving your ass a smack. "You were trying to get me all flustered in front of my teacher. Well I will not let you get away with that," your arms were bound behind your back from his rope tying, so you could do nothing to fight as he started to nibble at your breasts. You gave a small gasp and moan.

"L-Lock the door at least~" you got out, trying to act coy but he just smirked at you. 

"Oh no near, I want people to walk in," he used his finger knifes to cut the binding around you leg so he could spread your legs open. "i want people to see me fucking you over my desk like the little whore you are~" he purred as he rubbed your clit, being careful not to cut the little bundle of nerves. You gave a moan and chuckled at him. Nodding your head. He flipped you around, taking the cut in half piece of rope to tie your legs down to the different legs of his desk keeping them nice and open for him. YTou were drenched, so the need for foreplay was none. He grabbed the desk on the other side, his sharp nails digging into the wood before he pushed in with a single thrust. You gave a gasp and looked up at him. "This is for being for so naughty~" he warned as he started to go at it, thrusting in and out at a rough pace you hadn't seen from him before. Other than his bondage, he was rather gentle in bed. So you were seldom used to this rough pace he was taking right off the bat. He grabbed your hair and yanked it back, making you face toward the door. 

'Ah~ Dire~" you moaned only to get a harsh slap on the ass.

"Right now I am master, get it right little slut" he ordered. 

"Master~" you moaned out. He chuckled and gave another slap of the ass, going at a rougher pace. You felt him slamming against your cervix. Oh god, you gave a moan and bucked back. He looked at you and smirked. 

"Lash of Love!" he exclaimed, and then his cord wrapped around your throat. You gasped as he tightened it a little, choking you. You couldn't moan or do anything as he kept fucking you, oh god, everything was suddenly a hell of a lot more intense. You felt everything more vividly, the panic and adrenaline mixed with the pleasure was intoxicating. It was so much for you as you came on his cock, tightening around him. His cord disappeared, letting you breath as his finished, his warm cum going into you before he pulled out. He cut the binding of the rope all over your body letting you free. "I wasn't too rough, was I? I know it was a punishment but it still felt... rough." You shook your head and weakly kissed his cheek. He chuckled a bit and wrapped his cloak around you. "Go over the couch and rest my love, I will take you home after school," you nodded and stumbled over as he cleaned everything up. You shuddered still feeling his warmth within our womb.

You were going to have to tease him well he was working more often.

**Notes for the Chapter:**

> Crowley is a dirty bird


	10. 【Good Puppy】

**Summary for the Chapter:**

> Crewel needs some entertainment well grading papers.
> 
> Good thing he has such a sweet, and loyal puppy~

"C-Crewel," you cried out, watching your husband grade his classes papers, paying you no mind as you lay squirming on the bed a remote vibrator shoved inside you at just a high enough speed to drive you mad, but also not high enough to give any relief. You couldn't see his face, but you could tell he was grinning as he moved his hand to the rectangle remote on the desk and turned it up to full blast for just a few moments. You gasped and moaned, bucking your hips up getting so close. On the verge of you climax... You felt tears in your eyes.... before turning it off completely. You gave a cry, this time instead of in pleasure, sheer disappointment and tried to look at him. He chuckled a little.

"Now dear, puppies don't speak now do they~?" he asked, not even looking back. You gave a whine. "Do I need to go get the muzzle~?" he threatened. You shook your head and whimpered. Curse this cruel, kinky, sexy bastard you called your husband. You whimpered and squirmed within the chains. You needed a orgasm! At least some from of attention! You whined loudly, but that didn't seem to do much as he kept the vibrator shoved inside of you off. You puffed out your cheeks and started to pull on the chains making them rattle and started to whine louder. He gave a sigh and turned it onto the lowest setting. You sighed and laid back. Fine, he would be finished with his work soon enough. And you know once he saw you all chained down to the bed wearing his favorite, red leather collar, dripping wet with a toy inside of you... Well, he wouldn't be able to keep his hands off of you. That is if he ever finished grading his god damn papers!!! Of al the careers why did he have to pick teaching... 

Granted the idea of you being a naughty little student, failing his class as he offered you some very special extra credit to save you grade sounded really sexy now that you thought about it... You'd have to bring it up to him at a later date and ask if he would be into that. The scene of being over his leg and smacked with a ruler flashed through your head, oh ya, that would be hot. A bit of drool ran down your face as you thought of it.

"Well, well, I see you are really getting into the role of puppy, drooling all over the place like an actual dog," he slide two fingers under the collar and dragged you forward, a grin on his face. His other hand wiped the drool of your face. You smirked and gave his cheek a lick. He clearly was not expecting that, he recoiled back for a moment before a grin crossed his face. "Good puppy~" he gave you a kiss, he removed the toy that was inside you. You gave a gasp allowed his tongue to go into your mouth. You gave a muffle moan as you wrapped your tongue around his. He tasted like wine and his fancy cigarettes. He chuckled and pulled away. You looked up at him and he shook his head.

"You know you look gorgeous like that," he started to unbutton his vest, his coat already being abandoned on the chair. He went over the closest putting it on a hanger. You looked at him, very much not amused by him carefully putting away his clothing piece by piece. "All tied up like that, wet and dripping for m- hey, what is with that scorning face?" he asked. Oh he new exactly why you were glaring at him. 

"Fuck me already!" you exclaimed. He clicked his tongue and walked over, grabbing the ball gag from the nightstand. 

"I thought we had already had this talk. Dogs don't talk~' you rolled your eyes and opened your mouth. He put the gag on, he patted your cheek affectionately, not wearing his gloves. He walked over back to the closest and seemed to slow down the pace as he kept undressing. The chains rattled louder the longer it took as you got more agitated by the wait. He walked over to you and got on top. You looked up at him, trying to fake innocent eyes. He kissed your forehead as he slowly rubbed his cock against you wet, slippery folds. "Come on deary, beg for it~'

His grin quickly faded when he saw the look on your face. He shook his head, chuckling a little. 

"Alright dear, we can forgo the begging for tonight~" he purred and slipped it in. You gave a moan and bucked your hips upwards right away. "Eager, aren't we puppy~" he shook his head and grabbed your hips, setting a pace of quick and ruthless. "Very well, I think I have kept you waiting for master's cock long enough~" you gave a loud groan, if your legs weren't tied down they would be wrapped around his hips right now, dragging him deeper into you. Oh god no matter how many times you two had sex, it always felt good. His thrust were long and deep, rubbing right up against your cervix, your eyes rolled back into your head. He smirked and bit right into your shoulder, piercing the skin with his sharp canines. You yelped and rolled your hips up. You tightened your pussy around his cock. He gave a grin and gave a hard thrust. 

"Come on puppy, cum for me, we both know you want to~" he pinched your clit and that is what sent you over the edge. After a night of nothing but teasing, finally being allowed to cum felt like heaven. You screamed into the gag and fell limp under him. He chuckled a little. He held back a groan as he felt you get tighter around him. "I am so close, puppy" he whispered to you. With a few more thrusts he cam, giving a groan as he filled you up with his warm seed, he panted a little and pulled out. He laid down and looked at you. He removed the gag for you. 

"Was it good for you?" he asked. You nodded your head.

"Please unchain me," you said. He nodded his head and grabbed the keys, quickly clicking all four of the locks. You snuggled closer to him. "... wanna try a teacher x student roleplay?" he looked down at you and gave a laugh.

"Alright dear, we can try it this weekend~"


	11. 【Captured Mouse】

**Summary for the Chapter:**

> At one point you thought you could go home...
> 
> Crowley made sure that would never happen.

**Notes for the Chapter:**

> Reader is over 18 but this is a yandere Teacher x student.   
> Also I know we just had Crowley but who does not love the dirty birdy? Yandere dirty birdy no less.

The only light in the room was a soft blue nightlight that emitted from the corner. The only light source to show you, shivering on the bed. There was no window, no door, nothing more than an air vent yet still the room you found yourself in managed to be freezing. You were unable to cover yourself due to the handcuffs that kept your hands chained to the top of the headboard. Completely exposed your nipples, at this point, were hard enough to cut glass if you needed. Screaming for help was impossible with the red rubber orb crammed into your mouth. You were trapped in this room with no way out. Now, what got you in this position? The answer was rather simple. 

A question.

You had asked the wrong question at the wrong time and the man who had kept you down here, well, he did not like the question at all. So as punishment he tied you up and left you in the room. Normally you could at least read or do something to occupy your time... but instead you laid there stuck in bed with no way to do, well, really anything. Not that you could run to start with. Even when you had your freedom, you should have suspected that he was going to keep you here... He never took the job of sending you home all that seriously.

"Ah, dear, you look so good like that~" his voice echoed within the room before he appeared. Dire Crowley. He smiled and removed his mask and cloak, hanging them on a coat rack before flicking on the light. When you had first seen his face it was a shock that he had removed his mask, now it was simply a common vision. You sent him a small glare and he gave a sigh. "I know you are not happy I tied you up and left you here... but you know how I feel when you ask about them," he crawled on top of you and gave a kiss on top of the gag. You turned away and he furrowed his brows, he put a clawed hand under your chin and moved your face back to him. "No need to be so bitter dear," he rubbed his chin before his golden eyes lit up. "I know just how to cheer you up~! I was in a bad mood when you asked... but now that you have calmed down how about I answer your question," you looked back at him your eyes wide and he grinned nodding his head. "i suppose it was more than a little mean for chaining you up for something so simple, so I will tell you all about what has become of your friends... and give you a little reward for being so patient, because I am so gracious~" your expression fell as he got off of you. His 'rewards' were rarely all that good. He walked over the wardrobe in the room, which did not contain any clothes. he had deemed those unnecessary within the first month of your stay in this tiny bedroom like room. He walked back over with a grin on his face. 

"Now then, where to start..." he lit a candle on fire. "I suppose just in general, everyone does miss you. A lot in fact, some even asking if you will ever be back..." he licked his lips as he dripped a bit of wax on your chest. You gave a loud squeal and bucked your hips up. He chuckled a little. "Aw~ So cute dear." he chuckled a little and dripped some on your stomach. "Malleus has been more effected than you would think. He enjoys the Ramshackle dorm being opened again... but I suppose even someone like him gets lonely," you flinched when he brought up Malleus. You had... developed feelings for Malleus, even if you never acted on them for many reasons, mostly being you didn't think he would feel the same. And you two weren't the closest as two could be... but you did wonder what could have happened. The only person you had dared to tell about it?

The man who would later kidnap you, tricking you with the promise of your home. Dire Crowley,

He chuckled at your expression and kissed your cheek, running the wax over your thigh. He blew out the candle and placed it down on the nightstand near by. He reached over and grabbed a feather. He dusted it under your nose nearly getting a sneeze before leaving it, just letting you build up the sneeze with no real way to get rid of it. He chuckled at the discomfort on your face as he started to tickle your sides, coaxing a muffled giggle out of you.

"Hm... what else? Oh, yes, Deuce has taken it upon himself to work even harder, he hopes that when and if you come back he'll be able to tutor you to show off what he had learned," you squirmed in the grips as he ran the black feather over your side and under your arm pit, getting a loud giggle. "he still isn't.... well, what you would call bright, but his grades have been improving," he chuckled and dusted down towards in between your thighs, getting a loud gasp as you squirmed away, muffled laughter leaving the gag."Ace is another one who has been trying harder, though he does deny how much he misses you compared to the others," he dusted your clit with the feather, barely touching it yet still making you give a small gasp. He laughed a bit. "him and Grim don't fight as often anymore," he put down the feather and pulled out a small egg vibrator and held it up to your clit. Your whimpered as he turned it on, letting it buzz against it. You gave a loud cry.

"Lastly, Grim," he shook his head a little bit. "Grim is still a bit of a trouble maker... but he has calmed down a lot since you have 'gone home'. He was taken into the Ignihyde as his own student," he tsked a little as he turned up the setting a few notches. "He really does try to deny how much he misses you... but I sometimes I see him going near the Ramshackle dorm and simply stare," he smirked a little as you slowly started to unravel from the pleasure of the vibrator. He kissed you through the gag again and chuckled a little, moving close to your ear.

"I wonder what your friends would say... seeing you like this, moaning and drooling, wet for the headmaster~" he chuckled a little and bite you ears, you gave a small cry as he turned it up more, getting it to the higher setting. "Knowing you were so close to them... Moaning for me, cumming for me" he smiled and shook his head. Your vision fast white, he was still talking but you couldn't hear it as you came due to the vibrations. He clicked off the vibrator and used one of the many keys to unlock the handcuffs. he popped out the gag with a grin on his face. he got off the bed. You looked at him confused.

"What would you like for dinner? You have been tied up for awhile and I don't want you getting sick," you nodded your head.

".... Fried chicken sounds nice...."

**Notes for the Chapter:**

> If anyone wants a part two to these where Malleus and the dumb asses save you, let me know in the comments.


	12. 【Dragon's Hoard】

**Summary for the Chapter:**

> Crowley was so sure he had you
> 
> He was soon to be mistaken.
> 
> Part two of chapter 11.

**Notes for the Chapter:**

> You guys wanted it, you guys got it!
> 
> This is very, very long with some smut at the end. So I hope you all enjoy!

Grim stared at the book and his ear flattened against his head. He had finally gotten into some interesting classes, yet somehow they were still so boring to studying. Did he really need this? ' _now Grim, you better be good even though I am gone'_ (Y/n)'s words echoed through his mind and he grunted, putting the book down, hopping off the table. He walked over to his bed and laid down, curling up... it was too big for just him. Something was missing.

"Why would I listen to her? She isn't even here," he grumbled and stared at the wall. He hated this. He was the Great Grim! He couldn't be missing some- some HUMAN!... Yet here he was, moping over the disappearance of his first friend. He he pulled his tail closer. At first it wasn't so bad, even though it did suck losing his best henchmen... But now it just... hurt, he wanted her back. Maybe just seeing them one more time would make him feel better. His ears perked up. "That is it! The genius Grim has done it again!!!" Grim grinned as he hopped off the bed, his tail swinging in the air as he held his chest high. If all he needed was to see her one more time, that is what he would do!

Grim peeked around the corner carefully before he entered the hall of mirrors. He sat at the mirror and looked up at it. Now, he of course knew he couldn't follow you back to your world... not with help from Crowley which he was not going to suck up and ask   
for... But...

"Hey Mirror! Show me (Y/n)!" it looked down at him, a stone cold face on his face. Grim rolled his eyes a little bit. "Fine, Mirror Mirror, show me (Y/n) please" he drew out the please. The mirror's image changed from the face of the mirror to.... something Grim was not expecting at all. 

"Now dear, say ah~" Crowley held up the fork to your mouth. You looked away, covering your chest refusing to make eye contact with him. Crowley gave a small sigh, shaking his head and tasking a little. "We can't have you not eating...You have only finished half of the plate!" he exampled and used his other hand to force you to face him. You whimpered as he started to scratch near your jaw with his claws, causing them to bleed. You opened up to stop him from cutting into your cheek and he popped the bite of fried chicken, mash potatoes and corn in your mouth. "See? Was that so hard," he asked as he grabbed a towel, wiping the crumbles off your face. You stopped resisting and accepted every bite he gave you, eyes... empty as you stared at the smiling headmaster. he gave a small chuckle and kissed your cheek once the plate was empty, placing the plate down to the side. "I love you," 

"... I love you too," you choked down bile as you spoke, you simply wanted to avoid punishment... so it was best just to lie to him. He had a grin on his face as he brought your naked form into his lap. He nuzzled your hair, breathing in your scent. He gave a chuckle as he laid down, dragging you along with him. He whispered sweet nothings into your ears.

"Oh dear, I wish we could stay like this forever... but I need to take care of something," he stood up and grabbed his cloak, hat and mask. "I will come back soon~!" and with a snap of his fingers, he disappeared. 

Grim darted into one of the coffins out of instinct as soon as the image from the mirror faded, being able to peek out from the crack as the headmaster appeared in the room. Crowley looked around the room and hummed a little.

"I swore I was being watched..." Crowley sighed and shook his head. "Should make sure everyone on campus has gone to bed... it is well past curfew," the crow like man noted before he left the room. Grim waited a few minutes, his heart racing against his rib cage. He had to tell the others about this as soon as possible! He kept his ears high as he careful got out of the coffin and started to make his way towards the door. He crept around the hallways, keeping his sharpened senses aware of every sound, scent, and sight he could possible keep track of. He moved his way to the courtyard.

"Almost there..." he whispered to himself... only to hear the clicking of shoes on the pavement. He darted to the apple tree and hide behind it, peeking out ever so slightly... It was, as he expected, Crowley. The crow looked around the courtyard and started to make his way towards the tree. Grim swallowed hard.

Crowley looked towards the apple tree and walked towards it, peeking behind the base of the tree. He furrowed his brow and circled around the tree, not catching a glimpse of anything... when he heard a rustle in the trees. He looked up and, with a powerful blast of wind, the leaves all flew up, making anything that was blocked being seen, the thud of a few apples landed on the ground. He sighed and shook his head.

"I need to get some rest," he tsked and shook his head as he walked away from the apple tree.

Grim almost started crying as he clung to the stone railing and dragged himself up, watching as the headmaster walked into the hall... The great Grim had avoid tragedy once again through his genius! He jumped down, his butt swaying in the air as he walked away from the railing.

"Hey," Ace rolled over and gave a small whine. 

"Not yet Deuce...." Ace whined and shut his eyes. Ace put a pillow over his face as he felt himself started to get tapped on the eyes. "Just five more minutes, I swear I will not be late for class," 

"Hey! Get up!!!" Ace shoved the loud nose away from his ear... but then he felt heat.... Lots of it. it was starting to hurt actually- He shot up from the bed and gave a small scream as he started to pat out the sleeve of his PJs. He looked over to see Grim, his arms folded across his chest. Ace's shoulder's fell as he looked at him.

"Oh, it is you," 

"No need to have such a tone!" Grim hopped down from the bed. Ace laid back down making Grim growl a little. "Get up!!! This is important!!!" the cat exclaimed as he started to claw at Ace's leg, getting kicked off the bed.

"It can't be so important that it can't wait till morning," Ace replied. Deuce sat up in bed, rubbing his eyes.

"Grim? What are you doing here?" he asked. Grim looked over at him.

"I didn't know you two shared a room! It must be really loud every night...." Grim shook his head. "This is important and it cannot wait till morning! So get up, Ace!" Grim ordered. Ace sighed and got up, Grim was not going to leave and he had the energy nor the motivation to blast him out the window with wind magic. Deuce got up as well, going over to the little tea table that was in the room. Ace sat across from him and rubbed his eyes. Grim hopped up on the table and looked between the two.

"This has better be worth it or I am throwing you in the well,"Ace murmured.

"Alright, so, I went to the hall of mirrors to see if I could see a reel of (Y/n)," Grim started and was already stopped.

"If this is because you miss (Y/n), we do too, but we can't really... help you here," Deuce started. Grim glared at him and shook his head aggressively.

"No! I went to the mirror to see a reel of her, and well, the mirror didn't show me a reel of her at the school-"

"She isn't in this world anymore, the mirror probably can't show people who aren't in this world anymore, mystery solved, I am going back to bed," Ace got up.

"No! No! It didn't show me a reel! It showed me her in present time!" Ace looked back at him and sat down again. "The mirror showed me her in this room, it was like a really fancy bedroom! She was sitting there on the bed naked with all sorts of marks on her! And I am not even to the crazy part," Grim took a deep breath. "She was being feed by Crowley! He never sent her home! He has been keeping her in some, fancy prison!" Grim exclaimed, throwing his paws in the air. 

"Well then," Deuce got up, knocking his chair to the floor. "We better go save her!" he punched his hand, a grin on his face. 

"Are you stupid? What chance do have against THE headmaster," Ace asked.

"So we just leave her to be tortured by that creep!?" Grim exclaimed. Ace shook his head a grin on his face.

"Of course not, all we need to do is... rally the right person, and I know exactly where to find him!" Ace grabbed his magic pen off the nightstand, Deuce following suit with him. 

"And where do you three think you are going?" Riddle asked, a glass of warm milk in his hand. The three turned around to face him, expressions akin to a deer in headlights.

"Dorm leader..."

"Better question! Grim, why are you here? You are in Ignihyde now, I see no reason for you to come to Heartslabyul at 1 in the morning," at this point all three were sweating bullets as they looked at each other. 

"We just wanted to er... take a walk, get our mind off some things," Deuce lied. Riddle narrowed his eyes.

"Off with yo-"

'No! Look, Riddle we..." Ace paused and took a breath. "Riddle... we really miss (Y/n)... we... we wanted to go to the magic mirror and see if we could remember some of the good times we had with her, but... we are too embarrassed to ask, and even if we did what are the chances the Headmaster will say yes?" Riddle paused and looked at Ace. He bit his lip and gave a sigh.

"... Very well, I will let it slide this once," Riddle said. Ace grin and nodded his head.

"Thank you, Riddle,"

"But if I find out you were missing around it will be off with your heads! Do you understand?" All three nodded their head quickly.

"Yes Dorm leader Riddle Sir, very much understood," Riddle nodded his head and walked back to his room, his glass of milk in hand. "I have gotten too soft,"

"it is scary how well you lie," Grim noted as they exited the house of the dorm. Ace gave a grin and a shrug. 

"I am simply a good actor,"

Grim looked up at the Ramshackle dorm before them. "Why are we here?"

"Because, if we are going to get help, we are going to need it from the cream of the crop!" Ace exclaimed as he stepped forward. He cupped his hands over his mouth. "Malleus!!!"

The fae gave a sigh as he stopped in his tracks, hearing his name being called. Maybe he should just teleport away?.... no, they were his beloved friends. He would.... at least hear what they had to say. Plus there was a chance Deuce was there and he still felt like he owed him. He appeared before the three of them, his arms crossed.

"What are you three doing out this late?" he asked looking down at all three of them.

"Wait, weren't you a third year? What are you still doing here?" Grim asked. Malleus gave a small smirk and a shrug. 

"I am allowed to keep my secrets," in reality it was insisted upon by Lilia that he stay for another year or so... Just to get more used to human culture... and for some reason he actually agreed to it. Maybe it was the sense of nostalgia the school held despite him being here for a short three years.... But he knew that probably wasn't the answer to why he decided to stay yet another year. .. Plus admittedly only having to deal with one annoying servant was a lot better and a lot less another than dealing with a whole castle of annoying servants who never let him spend a minute alone. 

"Grim, you explain what happened," Grim nodded his head and went into detail of what he saw... and well.... the more he spoke the more green flame started to burn the grass around them as his eyes narrowed. 

"Are you lying to me?" Malleus asked.

'What? No! This is serious! We can't defeat Crowley! And I don't think anyone else can!" Grim exclaimed. Malleus nodded his head and picked Grim up by the ribbon, putting him on his shoulder. 

The group of four made it to the hall of mirrors. Malleus placed Grim down and looked forward.

"I can't wait till we kick this dirty birds ass!" Deuce exclaimed. Malleus looked back at him and snorted a little. Deuce paused and looked at him. "What is so funny?"

"You three will get in the way, I will be going in alone," Malleus assured. All three looked shocked and offended.

'What!? No way! We are going in with you!" Grim exclaimed, putting a foot forward. Malleus looked down at them with a closed eyed smile. 

"Oh? Well if you can free yourself from those vines feel free to join me," 

'What vi-" Ace gave a squeal as he was wrapped up in vines, Grim and Deuce following suit as they fell to the ground, struggling in the grip of the, luckily not spiked, vines. 

"i will come back with her, you three simply wait," Malleus stated as he stepped into a coffin, looking towards the mirror, he held a hand out. "Mirror, mirror, on the wall, taking me to the location of (Y/n)!" he exclaimed. Ace, Deuce and Grim squirmed around as they watched him disappear. Grim growled. 

"Mirror, show us Malleus!" he exclaimed.

"Well then, this is such a tiny room, but well decorated,' Malleus said. Crowley shot up and got off the bed, snarling. You followed suit and sat up, looking at Malleus with wide eyes. He gave you a tender smile, he was dressed up in his robes with his staff. 

"Lash of love!" Crowley exclaimed, Malleus laughed and held his staff up, catching the whip like magic as it wrapped around. He yanked forward dragging Crowley across the room towards him. Crowley growled and launched another one, wrapping around his throat which hardly seemed to affect the dark fae. He held a hand out and thorns wrapped around Crowley's thigh. The bird hissed and tried to move his leg, only for the thorns to dig deeper, droplets of his blood dripping down and onto the floor. 

"You are pathetic," Malleus said as he got the whip free and kicked Crowley across the face. Crowley held his nose before launching a fire ball at Malleus, which was easily taken out by Malleus' own green flame. "You touch what is mine and expect that to go any other way but me winning?" he pulled back a fist and punched Crowley in the face, he couldn't get away due to the thorny vine sticking into his leg. He tried to turn his attention it, launching a fire ball but it did not even effect the vine. "Realistically, I don't need magic defeat you.... but...." Malleus shut his eyes as Crowley used wind magic to send him towards a wall. he landed on the wall and jumped forward, his hand turning into a dragon claw as he slashed at his face. "I want to make sure you suffer," Crowley held his bleeding wound and peeked an eye open to try and look at the fae. Malleus launched a thorny vine through his stomach. Crowley vomited blood, the crimson substance turning the gray carpet a dark shade of crimson. Malleus gave a laugh as he looked at him. Crowley stared at him, barely even able to move. "you stood chance from the beginning. For most I would end your suffering... but I think watching you bleed out is for the best," Malleus turned his attention towards you with a smile on his face as he walked forward, offering you a hand. You held the blanket closed to your chest and took his hand. Malleus grinned and helped you off of the bed, using a bit of magic to secure the cloth to your body. 

"Am... am I dreaming?' you asked. Malleus pinched your arm, making you give a tiny squeak. You looked up at him as tears wield up in your eyes. "I-I can't believe it," tears started to stream down your face before it turned into full out sobs. You hugged close to Malleus' chest as you started to cry harder and harder. Malleus stroked your hair a smile on his face as he teleported back to the hall of mirrors, the vines unwrapping around Ace, Deuce and Grim. 

"(Y/n)!" All three exclaimed at once, getting up and running up to you. Grim hopped into your arms.

"I can't believe you are ok! I should note, I was the one who started this whole rescue mission to save you," you smiled and hugged the gray cat close. 

"How are you doing, your majesty?" you looked back at Malleus who stood at the doorway, leaning against it. You gave a chuckle and got up and kissed his cheek.

"Just fine, my king," it had been five years since what happened. Going home... well... going home was no longer on the agenda. You had become Malleus's wife and queen. Crowley had been replaced with a much more effective, less klutzy headmaster. Ace had become a sailor, with his wind magic making trips quick and being able to avoid all sorts of storms. Deuce, meanwhile, had become a IT guy, one of the best in the business(he still gets the often visit from Malleus whenever his virtual pet breaks). Grim lived at the castle as a magician(well, that is what he thinks. Really he is the royal lap cat and body guard to the queen). Malleus had sent you to therapy to work through... what had happened. The memories still remain but... You felt a lot better now. Malleus nuzzled your hair and gave a sigh. 

"God I love you," he kissed your lips. You smiled and kissed back. He nuzzled your neck and threw you on the bed, getting a little bit of a squeal as he got on top of you. A gust of wind shut the door and both of your clothing somehow disappeared. You chuckled and rolled your eyes, giving him a kiss.

"You are excited," you noted as he started to kiss your neck. He chuckled a little as he bit down, getting a bit of a squeal. 

"Oh I love that sound," you ran a hand through his hair, purposely brushing his horns, he shuddered a bit and grabbed your ass. You felt him rubbing against you.

"You are really excited," he was hard already. He chuckled and rubbed your clit before he slipped it in, giving slow, shallow thrusts. You gave a small moan and grabbed his horns tightly. He bucked harder down as he looked at you.

"I have been thinking about my beautiful bride all day, how do you" he gave a rough grunt as he went in deeper. "expect me not to~" you gave a gasp as you felt him rubbing your cervix. He felt so good inside you~ He rubbed hips a little before he started to pick up the pace. He started to leave a trail of hickies on your neck getting a loud whine and moan.

"M-Malleus! We have a party tomorrow!" you reminded as he gave a deeper thrust.

"Well then, I guess I should leave more~" he purred into your neck. You gave a gasp and bucked up, feeling him leave more, so you wouldn't be able to hide them all so easily. "I better make sure no one is able to steal you," you moaned as he went faster.

"N-no one is going to steal me!" you moaned out. He gave a small shrug., a pant leaving his lips.

"You can never be sure~" he purred and kissed you. You held his horns as he slipped his tongue into your mouth. You moaned as you tongues started to battle for territory, which he easily over took your tongue, it was barely even a fight if we are being honest here as he gripped your hips. He rubbed your clit with his free hand, getting a squeal from your lips. "Come on, Princess~ I am close~" he purred. "I want you to cum before me~" you moaned and bucked your hips up, rocking against him. He rubbed against your g-spot getting a scream as you were finally pushed over the edge. Feeling himself being gripped, Malleus lasted no more than a few more thrusts. You gave a small moan feeling him cum inside. He pulled out and laid beside you, bringing you close to his chest. You nuzzled up to his chest.

"..... you are so sweet, do you know that?" you asked, looking up at him, he shook his head and kissed your forehead.

"I am nothing when compared to you," a hand pinched your cheek, making you whine a little. He laughed at your protest and stopped, resting the hand in your hair as he gently stroked it. "now then, as you said, we have a party... we better be well rested for it," Malleus said. You weakly nodded your head and shut your eyes... Gently falling asleep in the arms of your husband. 

Malleus looked down at you and smiled. He wouldn't trade this sight for the world.... He rested his chin on your head and shut his own eyes, holding you as if you were a pile of gold. Nothing would ever harm his beloved again.

After all, what kind of dragon allows someone to touch his hoard?

**Notes for the Chapter:**

> I hope you liked part too!  
> Fluffy Malleus is best Malleus.


	13. 【Mating Season】

**Summary for the Chapter:**

> Jack has been acting more affectionate than normal
> 
> I wonder why

**Notes for the Chapter:**

> This took way to long to write I hope you all enjoy.

Jack squeezed your side and nuzzled your neck, just breathing in your scent. You gave a small giggle and kissed his cheek.

'What has gotten into your lately? you are not normally this cuddly," you noted as he started to kiss the crook of your neck. He gave a small growl as he looked up at you. 

"I am allowed to be more cuddly...." he mumbled, his cheeks bright red. You paused for a moment and kissed his head and started to stroke his hair, rubbing behind the ears. You noticed his tail start to gently wag, a quiet thunk being heard on the bed. You gave a small giggle.

"You are adorable, do you know that," he looked away almost right away and grumbled a little bit,

"I.... I am not," he said a little bit as he gave you a tighter squeezed around your waist, slowly moving his head down till his face was right in between your boobs. You blushed a deep shade of red but gave a small laugh as you started to rub his ears. His tail was starting to speed up it's rhythm on the bed as you kept petting his head. You giggled and rubbed his back.

'Are you in heat, my big boy?' you asked and his tail shot up in the air and his ears stood at attention, getting up right away as he looked away.

'H-how do you know?" he asked. You kissed his cheek and started to move down to his neck.

"I have read a thing or too... and if you need I will happily help you take care of it~"

And with that suddenly both of you were naked. It was almost as if he had used magic but the ripping and now pieces of cloth on the floor tell a completely different story. He had been clearly holding himself back and now? Well now with consent he is going to let go of all that self restraint he had been keeping for so long.

"Jack!" you exclaimed as he started to nibble on your breasts, growling something out of how he will buy you some new clothing as he moved his attention towards you, giving you a sloppy kiss as two fingers started to work your clit. You moaned and gave a gasp as he started to push both in at the same time, his large callous fingers stretching your inner walls wonderfully. You grabbed his hair as his smooth tongue started to overpower yours. He pulled away, a trail of saliva connecting your mouths before he started to give you kisses all around your face. He was absolutely frantic.

He turned you around once he felt he had done a good enough job and started to growl into your ear. 

"Are you ready?" he asked, his breath in your ear. Everything was going so shockingly fast, he had always been one to take things slower but you slowly nodded your head. He growled as he grabbed yours hip, impaling you on his large dick. You gave a gasp and gripped onto the sheets. he started to slowly push in till he bottomed out. You slowly started to rock your hips back after a few moments, giving him the go-a-head. 

His thrusts started out slow, even in his frantic state he was still taking you into account. You would give him a kiss but given your current... position it made it a little bit hard. 

"You can go a bit faster~" you assured. His eyes widen and nodded his head as he grabbed you hips, pulling you closer. You gave a loud moan as he made strong and fast shorts, leaving a constant pounding on your cervix ensuring it was going to be bruised. You gasped out as he pinched your clit, squeezing it tightly between two of his fingers. You rocked back into him as he started to work his magic even faster, giving you the time of your life, and from how he was acting? This was the time of his life as well. What sent you over was the inflating of his knot, you gave a gasp feeling spread in a mix of pain and pleasure before cumming.

Jack gave a grunt feeling everything get tighter around him before following suit, laying down on top of you. After a few moment his eyes widen realizing what he had done. 

"I am sorry, I, I didn't mean to lose myself. I meant to pull out be-" you reach behind and patted his cheek, making him stop as you lay there tired.

"i am on a pill and I am sure there is some magic plan B," you waved him off as you snuggled closer to the blanket. Jack nodded his head and slowly leaned down and held you close to him.

"Are you sure you are alright?"

"You worry to much,"

**Notes for the Chapter:**

> Well I was tagging this I learned knotting dildos exist.


	14. 【Contract】

**Summary for the Chapter:**

> You and Azul had made contracts before. He was always so sweet, giving you good deals.
> 
> Well, not this time.

**Notes for the Chapter:**

> Now that you got your fluffy Jack fic, back to your regularly scheduled dose of pure S I N.

"What do you think dear?" Azul smirked as he slide the contract across to you. You looked down and gave a small swallowed, you picked up the contract rereading the terms once again. the twins looked at you, standing on either side of Azul their golden eyes seemed to glow as they watched your ever little movement. The look in their eyes made you worried that any sudden movement would cause you to be bounced on. You placed the paper down and picked up the pen shaking a little. Azul and you had made contracts before... But more often than not he had simple terms, a kiss for him and the twins here, grab him something from Sam's shop, rather simple things for such rewards. However... This one the payment he wanted was going to be a lot harder to get. And... him and the twins were acting a lot different than normal, after if they were planning something... 

But he would never give you an impossible task, would he? 

You looked at the dotted line, taking a short breath and just like that, the black ink stained the paper in the shape of your name. A sight that was common for you are this point... And yet somehow felt much different than any other time you had done it before. Azul grinned and took the contract right away. He gave a small chuckle and stood up. The twin's both were clearly holding back laughter, you swallowed a little bit as you looked up at the three of them, a rather sadistic look in their eye. He bent down and held the staff under your chin. 

"Well dear, you better get going~ I look forward to you coming with my payment~!"

"Ah! Floyd! Please," you gave a loud cry, he gave a giggle as he pulled away from the bite mark that now was probably going to be scarred into your thigh due to his sharp, serenaded teeth. You gave a whimper and looked away from him as he gathered some of your blood on his fingers, his eyes sparkling like a child as he licked some of the blood that was dribbling down his chin. 

"Jade! She is so cute when she bleeds~!" he exclaimed. His brother smirked as he fondled your tits. You squirmed in your bonds, hands being tied behind your back with your school tie. Your uniform wasn't fully unbuttoned, it was simply a slow time during the Mostro Lounge so you had been pulled aside to fulfill a special clause in your contract. Floyd licked the blood off his fingers before taking another bite out of your thigh, just above the first on. You gave a loud cry out as he dug his teeth in deep. He started to suck. You gave a small gasp followed by a whine. You fell backwards into Jade who gave a small chuckle, tilting your chin up a little. The trail of drool that ran down your cheek was just adorable. He leaned down and gave you a kiss, being more gentle with his teeth than his twin was being. You gave a loud whine as you kissed back, trying to lean up into his gentle touch and away from Floyd's rough handling of you. 

"Now Floyd, don't drain her to much," Azul reminded, a smirk on his face as he looked up, very much enjoy the view before him. "If she passes out we will not be able to get to the main event," he licked his lips, what a wonderful main event that would be~ Floyd gave a small whine and nodded his head as he pulled away, letting the blood trickle down your thigh. Smirked a bit and moved your panties aside. Floyd quickly stopped his pouting when he noticed the whole new thing to taste right before him. He dove in, his freakishly long tongue finding it's way around your core quickly and spending no time for mercy. You gave an opened mouth moan which allowed Jade to dive his tongue in. The hand near your womanhood started to tease your clit, well the other hand kept fondling your breasts. you started to cry a little. It was all too much. Jade smirked and wrapped his tongue around yours before pulling away, dragging your tongue out into the open with nothing you could do to free your tongue away from his hold.

"Hm, (Y/n) dear I have a question I don't think of us has asked," you gave panted as Jade moved away, a long string of saliva connecting you. You panted out as you looked towards him, giving him only answers as moans as his twin works your pussy so perfectly. He was hitting everywhere he needed to, and with Jade himself working on your clit? You felt like you were losing his god damn mind. He gave a small chuckle. "Are you... a virgin?" he asked. Your head nodded eagerly to answer the question. Azul started to laugh a little. 

"Oh my. what an interesting turn of events! I thought when you signed that contract you had at least known a man," Azul smirked and beckoned you over. Jade picked you up, removing you away from the menstruation of Floyd's tongue(which caused the more aggressive twin to give a loud whine). He unzipped his pants as he took you onto his lap. "How does it feel knowing you are about to lose every form of your innocence at once~?" you tensed up a little making him laugh. Jade smirked and bent backward on the desk well Floyd unzipped his own trousers, allowing the large, gritty member to fly free, Jade following soon after him. Azul smirked and laid you down on Jade who wrapped his arms around your waist, making sure you couldn't move to much. You gave a very weak squirm feeling something long and hot poke your back side, before Floyd moved a hand under your chin, making your head face his cock. You froze in place.

You had never seen a cock before but you were pretty certain that one was bigger than average. Your weak squirming became a bit more before Azul grabbed both of your hips. At this point there was no way for you to move. You gave a small whimper shutting your eyes.

Azul was the first one to move, moving his dick into your throbbing hole. A small yell left your lips as he started to stretch you out, or, it nearly did. Floyd's members entered your mouth before you could even start to make sounds. You nearly gagged as he shoved himself right in, he barely even got a quarter of his cock in before you couldn't handle him... But that did not seem to bother the moray eel what so ever. Azul worked on bottoming out, making his way inch by inch inside you. You cried around Floyd's dick making him give a moan. Jade smirked and moved his hand down, pointing his dick upwards before he himself finally started to work your way inside of you. You started to sob loudly against. Floyd shivered a little bit at the wonderful vibrations you were sending through his dick. 

Before too long, both Azul and Jade had managed to settle inside of you. You panted loudly already covered in sweat and tried to move your arms, but they were still firmly tied behind your back. Floyd gave a small giggle as he was the one to make the first move, trying to cram more of his oversized dick into your mouth. You gagged around him which made him shutter as your already tight throat tightened even more around him. Azul sent him a small glare, he had given plans to let you adjust... But you did feel rather wonderful. He started to move his way in and out of you. You gave a moan.

Jade gave a chuckle as he felt your body tense up around him, it was nearly painful but he didn't seem to mind. He started to buck his hips up. You screamed a little bit, your anus being forceful dragged along for the ride as he move in and out. You weren't sure who you should focus on, all of them were so overwhelming. You slowly started to feel yourself give in, relaxing against Jade who smirked.

Floyd smirked as he was able to go deeper into your throat due to your sudden relaxation. You gagged and spit up on his dick, a mix of saliva and per-cum dripping out of your mouth. You swallowed around him and that is what did it for him. Floyd groaned as he released down your throat, giving you no choice but to swallow every last drop. He pulled out of your mouth smirking at the little droplets of his semen that rolled down your already fucked out face. And you still had away to go before his brother and Azul were done with you. He smirked and walked over to one of the chairs and sat down, watching as your eyes still followed him.

You were the next to cum, you gave a loud gasp as you suddenly tightened around both mermen who were abusing your poor holes. They both gave a groan as you game. Azul shuttered feeling the extra lube cover his cock. His cheeks were bright red but he still seemed to be smirking. He tightened his grips on your hips and started thrust in at a faster rate, letting out little moans and compliments as he did so. You shuttered, your body twitching from the orgasm that still had yet to pass. Azul gave a growl as he finally released into you. He pulled out slow, allowing the string of mixed cum to form before breaking a part. He looked down at the sight of his cum leaking out of your pussy well Jade made busy work of your ass and sighed. 

"What a wonderful sight~" he sat down on his chair as he watched. Jade shuttered feeling the mixture touch his cock, acting as a bit of extra lube. Jade moved closer to your next and bit down, he moved one of his arms away from your waist and started to rub your clit. You gave a loud squeal as he continued to pound into your anus.

"Come on, you can cum one more time for me, can't you~?" Jade purred into your ears. You weakly gave a nod. Jade smirked and nodded his head. "good girl~" he shoved two fingers into your stretched out cunt, using his thumb to work your clit. You gasped and squirmed in his hold. He gave a hard thrust and you came undone once again. You fell limp in his hold. Jade smirked and shoved the two fingers into your mouth, making you taste the mix of Azul and yourself together. Azul licked his lips as he watched. Jade gave a small grunt as he finally released, cum flooding your asshole as you lay there, panting tired. Jade sat up, pulling you off his dick and laid you back down on the desk. You looked at the three who had all gathered around you, smirks on each one of their faces.

"I am so glad you failed your contract, my darling~"


End file.
